Jiang Ru
2008
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Journal
Chinese Journal of Pharmaceuticals
Abstract
Ethyl trans-p-methoxycinnamate was transformed into ethyl (2R,3S)-2,3-dihydroxy-3-(4-methoxyphenyl)propionate(2) in 87% yield and 99%ee by osmium-catalyzed asymmetric dihydroxylation with 1,4-bis(9-O-quininyl)phthalazine as the chiral ligand. Compound 2 was then treated with thionyl chloride to give (4S,5R)-4-(4-methoxyphenyl)-5-ethoxycarbonyl-1,3-dioxathiolane 2-oxide in 85% yield, the latter compound is a key chiral intermediate for preparation of diltiazem .